Hydrochloric Acid → N-(4-Ethylphenyl)-2,3,5,6-tetrafluoroaniline

HRID 603336

반응식

HRID 603336 반응식
[F:1][C:2]1[C:8]([F:9])=[CH:7][C:6]([F:10])=[C:5]([F:11])[C:3]=1[NH2:4].[CH2:12]([C:14]1[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=1)[CH3:13].CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.Cl>O.C1(C)C=CC=CC=1>[F:1][C:2]1[C:8]([F:9])=[CH:7][C:6]([F:10])=[C:5]([F:11])[C:3]=1[NH:4][C:17]1[CH:18]=[CH:19][C:14]([CH2:12][CH3:13])=[CH:15][CH:16]=1

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 127862,3,5,6-TetrafluoroanilineHCID 153131-Bromo-4-ethylbenzeneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23676156Sodium t-butoxide

생성물 1

HCID 21938675N-(4-Ethylphenyl)-2,3,5,6-tetrafluoroaniline

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
85 °C

실험 절차

A mixture of 2,3,5,6-tetrafluoroaniline (4.5 g, 27.3 mmol), 4-ethylbromobenzene (5.0 g, 27 mmol), toluene (50 ml), sodium tert-butoxide (4.67 g, 48 mmol), tri-tert-butylphosphin (217 mg, 1.07 mmol) and bis-dibenzylideneacetone-palladium(0) (260 mg, 0.45 mmol) is heated under nitrogen to 85° C. for 15.5 h. The mixture is cooled to room temperature and water (30 ml), concentrated hydrochloric acid (20 ml) and hyflo are added. After stirring for 45 minutes, the mixture is filtered and the organic phase is washed with water three times. The solvent is evaporated in vacuo and the residue is chromatographed on silica using hexane/toluene (9:1 to 3:1) affording N-(2′,3′,5′,6′-tetrafluorophenyl)-4-ethylanilin as a liquid.

후처리

  1. temperatureThe mixture is cooled to room temperature
  2. filtrationthe mixture is filtered
  3. washthe organic phase is washed with water three times
  4. customThe solvent is evaporated in vacuo
  5. customthe residue is chromatographed on silica

출처 및 근거

ORD 기록
ord-db7c28842a0549feb90e747c0c7962f1
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906677B2

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